AI Penetration Tester
@ Crossing Hurdles

Hybrid
$222,000
Hybrid
Contractor
Posted 11 hours ago

Your Application Journey

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XXXXXXXXXX XXXXXXXXX XXXXXXX******* @crossinghurdles.com
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Job Details

About the Role

The AI Penetration Tester at Crossing Hurdles works with world-leading AI research labs to build and train cutting-edge AI models through adversarial testing strategies.

Key Responsibilities

  • Red-team AI models and agents using jailbreaks and prompt injections.
  • Generate quality human data by annotating AI failures and vulnerabilities.
  • Apply structured taxonomies, benchmarks, and playbooks for testing consistency.
  • Document detailed findings to produce reproducible reports and datasets.
  • Support multiple projects including LLM jailbreaks and socio-technical abuse testing.

Required Qualifications

  • Experience in AI adversarial work, cybersecurity, or socio-technical probing.
  • Expertise in adversarial machine learning including jailbreak datasets and RLHF/DPO attacks.
  • Cybersecurity skills like penetration testing, exploit development, and reverse engineering.
  • Ability to explore socio-technical risks including harassment, disinformation, and abuse analysis.
  • Creative skills using psychology, acting, or writing for unconventional methods.

Application Process

The application consists of a resume upload, an AI interview based on your resume (15 minutes) and a form submission (20 minutes) with flexible, asynchronous scheduling.

Key skills/competency

AI adversarial, cybersecurity, penetration testing, reverse engineering, LLM, jailbreaks, prompt injection, vulnerability annotation, socio-technical, creative probing

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How to Get Hired at Crossing Hurdles

🎯 Tips for Getting Hired

  • Customize Resume: Tailor your experience to AI red-teaming.
  • Highlight Tech Skills: Emphasize cybersecurity and adversarial ML expertise.
  • Research Crossing Hurdles: Understand their mission and client base.
  • Prepare Examples: Showcase successful adversarial testing projects.

📝 Interview Preparation Advice

Technical Preparation

Review adversarial ML techniques.
Practice penetration testing exercises.
Study cybersecurity exploit development.
Familiarize with prompt injection methods.

Behavioral Questions

Describe a challenging testing scenario.
Explain problem-solving during a project.
Detail working under flexible schedules.
Discuss adapting to changing requirements.

Frequently Asked Questions